The present invention is directed to a novel form of a pyrrolopyridine-2-carboxylic acid amide, which is an inhibitor of glycogen phosphorylase, compositions containing it and their use in therapy. The invention is also directed to processes for production of the novel form, novel intermediates used in said processes and processes for the production of said intermediates.
Inhibitors of glycogen phosphorylase are useful in the treatment of diabetes, hyperglycemia, hypercholesterolemia, hyperinsulinemia, hyperlipidemia, atherosclerosis or myocardial ischemia.
International Patent Application No. PCT/US2004/016243 (published after the priority date of the present invention) discloses pyrrolopyridine-2-carboxylic acid amide inhibitors of glycogen phosphorylase, including the compound 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid [1-(S)-(4-fluorobenzyl)-2-(4-hydroxypiperidin-1-yl)-2-oxoethyl]amide.
PCT/US2004/016243 describes the synthesis of 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid [1-(S)-(4-fluorobenzyl)-2-(4-hydroxypiperidin-1-yl)-2-oxoethyl]amide as the free base by amide coupling of either 2-(S)-[(5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carbonyl)amino]-3-(4-fluorophenyl)propionic acid and 4-hydroxypiperidine or 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid and 2-(S)-amino-3-(4-fluorophenyl)-1-(4-hydroxypiperidin-1-yl)propan-1-one hydrochloride in dimethylformamide in the presence of diisopropylethylamine.
It is desirable to obtain novel forms of this compound having advantageous pharmacological properties and to provide improved processes for the production of such compounds.